So, then the question is whether to stay in the Loop, near the Magnificent Mile, or somewhere else. The Loop is boring – it’s all office buildings – but there are a bunch of hotels there and you are near the Art Institute (a fantastic museum, definitely worth visiting). Millennium Park and the CSO (http://cso.org/) are also there. If Will (http://cso.org/About/Performers/Performer.aspx?id=6158) is in the house, say hi for me.

The Magnificent Mile is more touristy, both in a good and bad sense. There are lots of hotels (the Drake is a classic old place), shopping, and restaurants (but there are also some nice places sprinkled throughout the Loop), However, since it’s touristy is can seem a little bland and generic. The MCA (http://www.mcachicago.org/) is nearby, though, and pretty cool.

Chicago has very distinct neighborhoods, so you may want to stay a bit out of the center and get more of the local experience. For instance, Wrigleyville has lots of sports bars and clubs (because it surrounds the Cubs’ ballpark, Wrigley Field), while Andersonville is the old Swedish neighborhood. (It isn’t anymore but it’s still nice and fun to hang out – it’s a good place for brunch on the weekend.) Wicker Park is also popular. Pislen’s entirely Mexican and has great food. Chinatown (http://en.wikipedia.org/wiki/Chinatown,_Chicago) can also be nice for a meal.

Finally, as you may know, Chicago is known for improv, with lots of people from Saturday Night Live coming from Second City (http://www.secondcity.com/) and places like that. Well worth the ticket.